This invention relates to novel compounds, and more particularly to 11,11,12,12-tetracyano-9,10-anthraquinodimethane and its derivatives.
Heretofore, 7,7,8,8-tetracyanoquinodimethane (hereinafter referred to briefly as TCNQ) and 9,9,10,10-tetracyano-1,4-naphthaquinodimethane (briefly, TCNNQ) and various derivatives thereof (All of these compounds are collectively referred to as TCNQ and TCNNQ compounds) are known. These organic ompounds have excellent semiconductor characteristics and, as is well known, have great industrial values.
The molecular formulas of TCNQ and TCNNQ are presented hereinafter [(1) and (2), respectively]. TCNQ and TCNNQ, and various derivatives thereof have the tetracyanoquinodimethane skeleton represented by formula (3), and this skeletal structure is determinant of the characteristics of these compounds. ##STR2##
In this specification and the claims appended thereto, the term `tetracyanoquinodimethane skeleton` means the skeletal structure consisting of those carbon and nitrogen atoms which constitute the molecule of TCNQ.
TCNQ and its derivatives have been described in the literature including D. S. Acker, et al., J. Am. Chem. Soc., 84, 3370 (1962) and R. C. Wheland, et al., J. Org. Chem.,40(21), 3101 (1975).
The structural analysis of TCNNQ has been attempted and reported in F. Iwasaki, Acta Cryst. B27, 1360 (1971).